Why I Left My Big Fancy Tech Job and Wrote a Book

Several years ago, I was sitting in the audience at a big tech conference, learning about a startup that made it easy for people to rent rooms in other people’s houses for short stays. In a world where people can now travel to any part of the world and share someone else’s home, could we hope, the CEO asked, for greater cross-cultural understanding? “Would nations have less war if the residents lived together?”

I closed my eyes, breathed deeply, and felt an immense sense of peace and hope for humanity wash over me.

Then I opened my eyes and thought, “Isn’t this basically a hotel in someone’s house — a cool, convenient, unregulated hotel?”

When it was my turn to take the stage, I too had a grandiose proclamation: Our startup, I declared, was helping people make meaningful connections in the real world.

What I really should have said was: We help people hook up.

On the plane ride home, I began to write what would eventually become The Big Disruption, a satirical novel based on my experience working at both a startup and one of the biggest tech companies in the world. I had no goal at the time other than to provide a bit of cathartic escape from the tech industry, where, on the surface, things seemed really important and exciting.

We were doing big things!

Bringing the internet to the developing world!

Singing songs to orphans!

But also, on some level, it all felt a bit off.

So, where to begin?

Should I start with the early stage companies? Like the time I was at a startupand the founder I was working for — a guy who owned a hundred shirts in the same color and quoted Steve Jobs on a daily basis — asked me whether we should hand out dildos as company swag or consider converting our social media platform into an anonymous sex club. (We even whiteboarded it.)

Or maybe I could start with the money — all the absurd valuations with seemingly little basis in reality. Or the time a partner at a VC “jokingly” offered up my female friend, his employee, as an enticement for a founder to work with his firm.

You can’t really claim that you’re building for everyone in the world when your own workforce doesn’t remotely resemble the outside world.

Or maybe I should start with the tech workers. The employees at my most recent job — running PR at a huge tech company — were some of the smartest, most passionate people I’ve ever worked with. They worked through the night to help people in a natural disaster. They gave money and vacation time to help the sick family members of other employees. They ran marathons on the weekend to raise money for clean water in Africa.

They also spent the weekday complaining on company message boards about the brand of water stocked in the micro-kitchens.

Then there are the amazing products. The progressive politics. The mighty ethical stands against evil. These are the things that, in my twenties, pulled me to tech in the first place and made me think I was embarking on something truly different.

To be sure, Silicon Valley has built some great products that have truly changed our lives for the better. And I do think that in many, many ways, it has taken noble stands during difficult times and helped redefine what people expect from companies, well beyond just the tech industry. It has also led me to some of my best friends and greatest opportunities, for which I am very grateful. There is so much I really do love about this world.

But there is also what drove me to leave the big tech company last fall and take a break. The issues that I got tired of defending at parties. The endless use of “scale” as an excuse for being unable to solve problems in a human way. The faux earnestness, the self-righteousness. All those cheery product ads set to ukulele music.

I wrote this book for two reasons. First, I wanted to explore what drives the insatiable expansion of the big tech companies. Despite how the industry is sometimes portrayed in the media, I don’t really think the management teams at Facebook, Google, Apple, Uber, or Amazon wake up each morning thinking about how to steal more user data or drive us all out of our jobs. Those are real consequences, but not the root cause. Rather, it’s the desperation to stay on top and avoid being relegated to a dusty corner of the Computer History Museum that pushes these companies into further and further reaches of our lives.

Second, I wrote this book because we should be able to love and celebrate the products that we build — but without ignoring the hard questions they raise. We need to end the self-delusion and either fess up to the reality we are creating or live up to the vision we market to the world. Because if you’re going to tell people you’re their savior, you better be ready to be held to a higher standard. This book is my small way of trying to push us all to be better. Meaning…

You can’t tell your advertisers that you can target users down to the tiniest pixel but then throw your hands up before the politicians and say your machines can’t figure out if bad actors are using your platform.

When I wrote this novel, I eliminated almost all women and people of color from the story to make a point.

You can’t buy up a big bookstore and then a big diaper store and a big pet supply store and, finally, a big grocery store, national newspaper, and rocket ship and then act surprised when people start wondering if maybe you’re a bit too powerful.

And you can’t really claim that you’re building for everyone in the world when your own workforce doesn’t remotely resemble the outside world.

When I wrote this novel, I eliminated almost all women and people of color from the story to make a point. It’s an exaggeration — the book is satire, remember — but it’s also true that the Valley has a diversity problem.

Would Uber have had such a toxic internal culture, rife with sexual harassment, if there had been more women on the management team helping to drive the company’s culture? Would the Google Photos app have labeled the image of an African-American woman an “ape” had there been greater representation of African-Americans on the engineering, product, or quality assurance teams — someone who might have questioned whether the data pool feeding into the algorithm was sufficiently diverse? Would we see more funding for technology tackling problems affecting lower-income communities if venture capitalists were not graduating from just a handful of elite institutions?

That’s also why I ultimately decided to publish this novel under my name. I was very tempted to publish it anonymously. I didn’t really want the attention for myself, and I didn’t want people to interpret the book as a specific take on one company. (For the record, I wrote it when I was between jobs.) Nor did I want readers to sit diagramming the characters, trying to figure out which character corresponded to a famous tech exec. (Hint: None of them do, except the one likable character. Clearly, that’s me…just kidding. No one’s likable in this book.) But at a time when tech is under scrutiny for a number of issues, it’s important that those of us who can speak up publicly do so without the comfortable cloak of anonymity.

Writing satire feels a bit like trimming a bonsai tree with a machete. But it felt like the right approach for an industry that takes itself far too seriously and its own responsibility not seriously enough. Because sometimes you’re not saving the world; you’re just building an anonymous sex club. And that’s fine — I’m sure there are plenty of people who like anonymous sex clubs — but let’s just be honest about it.

Stop trying to convince us — and yourselves — that your dildos are diamonds.